Vacation Rentals


Properties Available 38 properties available
Welcome to Sea La Vie Beach House!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals2825 sq. ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower, Double Vanity, & Soaking Tub- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower- 1 Queen
Hot HOT 54
Sea La Vie Beach House
Anna Maria
$600.00 - $2,200.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (2)
Welcome to Beachy Villa Vista!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.2177 sq ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining seating 12, Living w/ TV- Plenty of outdoor deck and patio space including covered lanai- Deck with Gulf &am
Hot HOT 19
Beachy Villa Vista
Holmes Beach Pet Friendly
$450.00 - $1,400.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 10 guests
Welcome to She's Always Right!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation RentalsThis spacious, bright, and luxurious island home is ready to bring some laughter and memories to you and your group! This home is located just a quick skip to the beach, local restaurants, shops and centrally located on the island!
Hot HOT 55
She's Always Right
Holmes Beach Pet Friendly
$359.00 - $1,500.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (12)
Welcome to Seaswept Mermaid!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals2512 sq. ft.Need more room? Reserve the sister 4 bedroom home next door, Salty Pirate (#1678416), to stay at The Pirate and His Mermaid homes for a total of 8 bedrooms!HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV, Ple
Hot HOT 17
Seaswept Mermaid
Anna Maria
$420.00 - $1,450.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (6)
Welcome to Coconut Lagoon!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Ground Level Completely Updated Luxury Historic Home3 Bed (sleeps 6), 2 1/2 Bath with Heated Pool easy walking distance to Pine Avenue and Gulf side beachesHIGHLIGHTS:- Kitchen, D
Hot HOT 36
Coconut Lagoon
Anna Maria Pet Friendly
$320.00 - $920.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
Welcome to On Turtle Time!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Beautifully Recently Updated Ground Level Home w/ Private Pool in Holmes Beach, 6-8 min walk to beachNOW OFFERING UP TO 40% OFF* SUMMER RATES   *price reduction a
Hot HOT 25
On Turtle Time
Holmes Beach
$260.00 - $720.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
Welcome to Cozy Cabana East!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Renovated Pristine Home w/ Private Pool in Holmes Beach, 6-8 min walk to beachHIGHLIGHTS:- Kitchen, Dining, Living w/ Queen Sleeper Sofa & TV- 1 King Bedroom, En-Suit
Hot HOT 14
Cozy Cabana East
Holmes Beach Pet Friendly
$240.00 - $750.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
Welcome to Fins Up!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.New Home w/Private Heated Pool & 4 Min Walk to Beach w/Beach Gear!1250 sq. ft.HIGHLIGHTS: - Kitchen, Dining, Living w/ Soaring Ceilings & Queen Sleeper Sofa & TV- 1 Ki
Hot HOT 11
Fins Up
Holmes Beach
$300.00 - $750.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (9)
Welcome to A Wave From It All!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower/Tub- 1 Queen Bedroom w/ TV, En-Suite Full Bathroom
Hot HOT 27
A Wave From It All
Anna Maria Pet Friendly
$320.00 - $890.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (8)
Welcome to Mariner's Crossing!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.A newly constructed premier luxury home just across the street from the pristine sugary white sands of Anna Maria Island with views of the gulf from practically every
Hot HOT 20
Mariner's Crossing
Bradenton Beach
$800.00 - $2,800.00 / per night
Bedrooms 8 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 5 (4)
Welcome to The Cottage on Pine!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Ground Level Fully Renovated Beach Cottage in Heart of Anna Maria2 Bed (sleeps 4), 1 Bath with Heated Pool directly on Pine Avenue. Short walk to Piers, Shops, and Gulf Side
Hot HOT 19
The Cottage on Pine
Anna Maria Pet Friendly
$290.00 - $800.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (3)
Welcome to Salty Pirate!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.2512 sq. ft.Need more room? Reserve the sister 4 bedroom home next door, Seaswept Mermaid (#1850215), to stay at The Pirate and His Mermaid homes for a total of 8 bedrooms!HIGHLIGHT
Hot HOT 14
Salty Pirate
Anna Maria
$360.00 - $1,000.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (5)

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